Technology Process of (1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.13,7]pentacosane
There total 30 articles about (1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.13,7]pentacosane which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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![(1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.1<sup>3,7</sup>]pentacosane](/Databaselist/images/loading.webp)
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213768-39-9
(1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.13,7]pentacosane
- Guidance literature:
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With
N-iodo-succinimide; silver trifluoromethanesulfonate;
In
dichloromethane; toluene;
1.) -45 deg C, 20 min, 2.) 30 min;
DOI:10.1021/jo9806097
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213768-39-9
(1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.13,7]pentacosane
- Guidance literature:
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Multi-step reaction with 11 steps
1: 84 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) o deg C to room temperature
2: 86 percent / TBAF / tetrahydrofuran / 9 h / Ambient temperature
3: 84 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 19 h
4: 80 percent / p-TsOH / methanol; ethyl acetate / 48 h
5: 1.) Bu2SnO, 2.) Bu4NI / 1.) MeOH, reflux, 2.3 h, 2.) tluene, 65 deg C, 15 h
6: 73 percent / pyridine / CH2Cl2 / Ambient temperature
7: 82 percent / NIS, triflic acid / CH2Cl2 / 0.5 h
8: 81 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 7 h
9: 61 percent / NaH, Cs2CO3 / tetrahydrofuran / 24 h / Heating
10: 1.) t-BuOK, 2.) HgO, HgCl2 / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H2O, 30 min
11: 62 percent / NIS, AgOTf / CH2Cl2; toluene / 1.) -45 deg C, 20 min, 2.) 30 min
With
pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9806097
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213768-39-9
(1S,3R,4R,5S,6S,7R,20R,22S,23S,24R)-4,5,6,24-Tetrakis-benzyloxy-23-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-22-methoxy-2,9,18,21,25-pentaoxa-tricyclo[18.2.2.13,7]pentacosane
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 55 percent / pyridine; CH2Cl2 / Ambient temperature
2: 82 percent / pyridine; CH2Cl2 / Ambient temperature
3: 84 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 19 h
4: 80 percent / p-TsOH / methanol; ethyl acetate / 48 h
5: 1.) Bu2SnO, 2.) Bu4NI / 1.) MeOH, reflux, 2.3 h, 2.) tluene, 65 deg C, 15 h
6: 73 percent / pyridine / CH2Cl2 / Ambient temperature
7: 82 percent / NIS, triflic acid / CH2Cl2 / 0.5 h
8: 81 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 7 h
9: 61 percent / NaH, Cs2CO3 / tetrahydrofuran / 24 h / Heating
10: 1.) t-BuOK, 2.) HgO, HgCl2 / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H2O, 30 min
11: 62 percent / NIS, AgOTf / CH2Cl2; toluene / 1.) -45 deg C, 20 min, 2.) 30 min
With
pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9806097
